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Agile Software Transformation Part 1: Plans versus Planning

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Agile Software Transformation Part 1: Plans versus Planning
Stephen de Villiers Graaff
Agile Coach and Consultant, DVT

Agile Software Transformation Part 1: Plans versus Planning

An Agile transformation is not like a product you buy off the shelf and install in your business. It’s a long, sometimes rigorous journey, often fraught with unexpected challenges and constantly changing landscapes. In this three-part series, DVT’s Agile evangelist Stephen de Villiers Graaff explores three definitive facets of the Agile mindset, told vividly though unique and colourful stories from contemporary history.


The American Civil war was never short of rambunctious characters making a name for themselves, often for the wrong reasons.


One such standout was General George Pickett, a career United States officer in the Confederate States Army. Pickett’s not-so-shining moment came in the infamous Battle of Gettysburg.


On the evening of July 2, 1863, Pickett’s charges and their Union counterparts happened on a field in Gettysburg, the Confederates on the one end, the Union on the other. It was a stalemate; something had to give.


General Lee, the Confederate Supreme Commander, presented Pickett with an ingenious plan to break the deadlock.


Lee proposed to open up with a canon barrage and lay waste to the Union front lines. With 168 cannons it would be the largest cannon barrage in the history of warfare at the time. The second act would be a simultaneous pincer attack from the left and right of the Union flanks. This would perceivably soften the centre of the Union ranks as they struggled to fight off the coordinated attacks. To create more confusion, they would also attack from the rear using cavalry.


At that point, at the height of this absolute carnage, George Pickett would take his entire brigade of 12,000 men straight across the field, straight through the middle, and quite literally split the Union.


It was an amazing plan. An incredible plan. A plan that couldn’t fail. And every part of the plan was executed. Then it all went wrong.


First came the cannon barrage, a deafening, remorseless sound that shattered the silence for miles, but with one simple yet fatal hitch: the Confederation didn’t take into account the height of the ridge above which the Union lines were perched (prophetically called Cemetery Ridge). And so the barrage by and large overshot the Union lines. It blew the Union’s support and medical tents to oblivion, everything behind the line was decimated, but the line itself wasn’t touched.


Then, the pincer attacks began, but for some reason they didn’t happen simultaneously, so the Union could fight them off left and right, then settle back in the centre.


The cavalry attack happened too, through the wasteland created by the cannon barrage. It was fought off by a precocious young Colonel called George Custer, the same George Custer who, as a General, went on to kill himself and all his men at the Battle of Little Big Horn. But I digress.


Tick, tick, tick, all the pieces of the plan, all on cue.


It was time for George Pickett to deliver the coup de grâce. Legend has it that he inspired his men by shouting, "Up, Men, and to your posts! Don't forget today that you are from Old Virginia." And so he took his 12,000 men across that open field in Gettysburg, to their deaths.


The field, imperceptibly, was at a slight incline, which slowed down the confederate charge. The Union forces, having spent the preceding minutes watching cannonballs flying overhead, had not moved. They patiently took aim, and shot the onrushing Confederates to smithereens. About 300 of the charging thousands made it to the other side of the line.


Lee and Pickett’s plan was well thought out and perfectly executed. But it didn’t account for change. At all. At any stage of the battle. It was rigidly applied, and the result was catastrophic failure.


Many years later, at the height of the second World War, Dwight D. Eisenhower remarked: “In preparing for battle I have always found that plans are useless, but planning is indispensable." The very idea of plans versus planning is one of the first things that needs to change for any organisation looking to adopt the Agile mindset.


Plans are static. No sooner have you clicked ‘Save’ on your Microsoft Project file than that file is outdated. All you’ve done is establish a baseline, and with constant change you’ll be constantly baselining. Planning, on the other hand, is an activity. It’s something that has to happen all the way, throughout your journey, at every step.


Fortunately, you have the benefit of hindsight. George Pickett didn’t, and paid the ultimate price.




An Agile transformation is not like a product you buy off the shelf and install in your business. It’s a long, sometimes rigorous journey, often fraught with unexpected challenges and constantly changing landscapes. In this three-part series, DVT’s Agile evangelist Stephen de Villiers Graaff explores three definitive facets of the Agile mindset, told vividly though unique and colourful stories from contemporary history.